3.1.7. Triene 26

This triene was prepared analogously as 25 from aldehyde 22 (47 mg) and Ph₃P=CHCOMe (55 mg; 2.0 eq) as a colorless oil in 76% yield (36.5 mg) (Figure 8).

The structure of triene 26 and the numbering of the atoms.

¹H NMR δ: 7.36–7.19 (m, 20H, arom.), 6.78 (dd, J = 16.3, 6.5 Hz, 1H, H-9), 6.46 (dt, J = 16.2, 10.6 Hz, 1H, H-2), 6.28 (t, J = 11.1 Hz, 1H, H-3), 6.18 (d, J = 16.2 Hz, H-10), 5.45 (t, J = 10.4 Hz, 1H, H-4), 5.27 (d, J = 16.7 Hz, 1H, H-1), 5.11 (dd, J = 10.0 and 1.7 Hz, 1H, H-1′), 4.85 (d, J = 11.4 Hz, 1H, OCH₂Ph), 4.64–4.56 (m, 4H, 3×OCH₂Ph and H-5), 4.53 (d, J = 11.4 Hz, 1H, OCH₂Ph), 4.45 (d, J = 11.6 Hz, 1H, OCH₂Ph), 4.32 (d, J = 11.7 Hz, 1H, OCH₂Ph), 4.18 (d, J = 11.6 Hz, 1H, OCH₂Ph), 4.15 (ddd, J = 6.5 and 5.3 Hz, 1H, H-8), 3.81 (t, J = 4.8 Hz, 1H, H-7), 3.70 (dd, J = 6.3 and 4.3 Hz, 1H, H-6), 2.11 (s, 3H, H-12);

¹³C NMR δ: 198.2 (C-11), 144.7 (C-9), 138.6, 138.3, 138.1 and 137.8 (quat. benzyl), 134.1 (C-3), 132.6 (C-10), 131.7 (C-2), 128.5−127.4 (arom. and C-4), 120.3 (C-1), 81.7 and 81.6 (C-6 and C-7), 79.3 (C-8), 2 × 75.3 (C-5 and OCH₂Ph), 74.0, 71.3, 70.3 (3×OCH₂Ph), 26.9 (C-12).

HR-MS: m/z = 625.2936; calcd for C₄₀H₄₂O₅Na [M + Na]⁺: 625.2930.